Launched in 2001, Crossroads at Marin Academy is a tuition-free academic support and enrichment program for middle school students who attend San Rafael public schools. The program was created in response to the challenges that many children in our neighboring communities face. Recognizing the developmental importance of the middle school years, Crossroads, in partnership with Venetia Valley and Davidson Middle Schools, identifies ambitious and motivated rising seventh graders and works with them over the course of two years. During this time, the program aims to reinforce academic skills; build self-confidence; develop aspirations for college and careers; and promote responsibility, integrity, and leadership. Each year the program includes an intensive summer component, held in collaboration with Aim High, an organization that has over thirty years of experience in providing summer learning opportunities for students from low-income households in the Bay Area. Crossroads also challenges Marin Academy students to engage with the larger San Rafael community in exploring and addressing issues of educational equity. During the school year, tutoring sessions and enrichment classes are led by MA students who join Crossroads as either tutors or Crossroads Fellows. Through their participation in the program, MA students are challenged to step into leadership roles as they build relationships with the middle school students and take on the task of designing lessons and leading classes. The program is privately funded and depends on the volunteerism of the Marin Academy community.